Prior efforts to incorporate multi hydroxyl containing amino compounds, known as glycol amines or amino sugars, into polymer substances have been described by others. A few examples of such compounds are glucamine and alkyl glucamines, for example N-methyl glucamine (NMG), glucosamine, alkyl glucosamine and tris hydroxylmethyl amino ethane (THAM). Typically this is done by trying to synthesize glycol amine-functional reactive monomers that can be polymerized or alternately by modifying existing polymers to incorporate glycol amine functionality. The most common synthetic route is to attempt to react a glycol amine with epoxy functionality in an existing monomer or an epoxy functional polymer. The problem with such a route is that glycol amines and amino sugars are typically high melting point crystalline materials with poor solubility in any material other than water or very polar solvents. Modification steps are typically inefficient and difficult to arrange without proper reaction media. Also, in water or polar solvents, ring opening polymerization of epoxy groups is a very likely undesired side reaction competing with the desired selective single ring opening of epoxy by amino group.
Another method reported for synthesis of polymerizable amino sugar monomers is to react available amino groups with acryloyl chloride to form an acrylamide structure. One problem is that acryloyl chloride is not readily commercially available and is a strong lachrymator that is difficult and dangerous to store and handle.
Yet another method for incorporating amino sugars into reactive monomers or polymers is to use the amino group to neutralize carboxylic acid functions. In this case, the amino sugar is ionically incorporated into systems which may provide useful properties for some applications but is not optimal for others.
None of these methods are ideal nor are they the most desirable commercially to practice. Among the prior art methods are those disclosed in U.S. 2010/0092782, U.S. 2010/0129755, U.S. Pat. Nos. 6,552,103, and 7,094,349.
It is well known in the art that low molecular weight primary and secondary amine compounds, including hydroxylamine compounds, that are liquid or have low melting points and are soluble in acrylates may be readily reacted into acrylate compositions by Michael addition, to the alpha, beta unsaturation of a multifunctional acrylate monomer. However, an effective, solvent-free method of reacting crystalline solid amino sugars which have higher melting points and very limited or no apparent solubility in acrylate-functional materials with acrylate compounds has not been described in the prior art. There is a need in the art for such new products and a solvent-free method of preparation by reacting said crystalline multi-hydroxylamino compounds.
There is also a need for reactive monomer compositions which may be used as novel surfactants, preparing adhesives, sealants, and coatings, including, without limitation, UV curable compositions.